We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pineland Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
58 rentals in Pineland.
Sort by:
Tripadvisor Sort

1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

*** LAST MINUTE SPECIAL ON JANUARY 2ND TO 9TH!!! INQUIRE TODAY!!! ***

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Bluefin Beach House

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Rockstar Beach House North Captiva Island (Accessible by ferry boat only)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Perfect Distancing Opportunity with Uncrowded Beaches, Hiking, Biking, Kayaking

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Serendipity - Pool, 2 Golf Carts, NCIC, location, location, location!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Oceanfront Luxury Home with Secluded Private Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beachfront, Pet Friendly Home, Free Cancellation - 202

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

NEW RENTAL*LUXURY HOME*STEPS 2 OCEAN* OVERSIZED POOL*LOCAL OWNERS*LO FEES

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Tropical paradise awaits at the Blue Tortuga

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Pineland rentals sent straight to your email!

Beach's Edge, One Of A Kind Beachfront Experience

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Perfect Placement, Beautiful Ocean Front Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Las Olas, 360* Ocean View, close to the best Beach on Island!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Windows on the Water 'W.O.W' A new ocean front oasis! Come enjoy the view!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Hidden Treasure - Secluded NEW Home - Pool-Tiki-Basketball- Near Beach- Club Use

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

New luxury home, 2 min to beach, 360 water views, club amenities

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

'Sea Urchins' ***** Private Property Beachfront with Beachside Pool & Boat Dock

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Easy Walk to Beautiful Beach, Sleep 10 In Beds, Watch the Sunset From Your Deck

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Newly Renovated Island Pool Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

BEAUTY & THE BEACH - LUXE BEACHFRONT MANSION, WEDDINGS, HEATED POOL, BOAT SLIP

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Paradise Found/ North Captiva / Heated Pool

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Island Oasis/Hidden Beach House-Private pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

FLORIDA AT THE BEACH, NEWLY REMODELED 2021- BEACH -OCEAN VIEW- GOLF CART

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beachfront, Pet Friendly Home, Free Cancellation - 201

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Captiva Beach Sunset ~Gulf front, private pool, 5 BR, NCIC & Airstrip Membership

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Waterfront Property with Dock and 2 Minute Walk to the Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Perfect Beach, Private Pool and Hot tub. Best Beach Sunset Views on the Island.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Remember When, Old Florida Beach House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

SEA LA VIE- BEACHFRONT-Large & Private, sleeps 10+Club Membership, 2 golf carts

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Under New Management-SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Sleep 7

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Romantic beach cottage with golf cart kayaks and bikes. Remodeled Coastal charm

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Bayfront Beach Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

LAST MINUTE SPECIALS, PRIVATE BEACHES, COME GET AWAY! HEATED POOL & PRIVATE BAR!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Vitamin SEA 365. Off the grid Bliss. Private Beach and Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Steps from the beach, Gulf and Sound Views, Pool and Cabana

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Nice spacious & charming home. Kayak, golf carts , bikes & free wine included.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

PEACE OF PARADISE - Private Resort Style Pool & Private Beach Access - Sleeps 10

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Near beach, includes golf cart , bikes , kayaks and pool , 5 stars, Boat Slip !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Second Star is nestled in palms and just 800' to the beach overlooking the lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

13 Sunset Captiva 2 Bedroom / 2 Bath House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

NEW LISTING! SERENITY NOW, SLEEPS 14, 4 KINGS, SCREENED-IN HEATED POOL, CLUB

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Welcome to paradise! You're now on island time!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Luxury private pool home, stunning views, just steps to beach on Captiva Island

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Island Queen, Luxury in Paradise, 200ft to Beach

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Doc Holiday - ‘Old Florida’ Cottage, 600 ft frm beach, Sleeps 8 in beds, pets ok

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Coconut Castaway | New Rental, Newly remodeled, Ocean Views, Hot Tub, Golf Cart

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Cottage Secluded in Palms 2 minute walk to Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Newly Built Floridays, Pool, Beachview, Lots Amenities

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
12
Frequently Asked Questions about Pineland